6371. 1-Naphthaleneacetic Acid

Nomenclature

CAS number: 86-87-3
α-Naphthaleneacetic acid; naphthylacetic acid; NAA; Fruitone-N (Rhone-Poulenc); Planofix (Hortichem); Tre-Hold (Amvac).
C12H10O2; mol wt 186.21.
C 77.40%, H 5.41%, O 17.18%.

Description and references

Prepn from naphthalene + chloroacetic acid: Ogata, Ishiguro, J. Am. Chem. Soc. 72, 4302 (1950); Southwick et al., ibid. 76, 754 (1954); US 2655531 (1953 to FMC); from naphthylacetonitrile: Wenner, US 2489348 (1949 to Hoffmann-La Roche); J. Org. Chem. 15, 548 (1950). Activity: F. E. Gardiner et al., Science 90, 208 (1939). Crystal structure: S. S. Rajan, Acta Crystallogr. B34, 998 (1978). Toxicity study: G. W. Bailey, J. L. White, Residue Rev. 10, 97 (1965).

Chemical structure

Properties

Needles from water, mp 134.5-135.5°. Sol in about 30 parts alcohol; freely sol in acetone, ether, chloroform. Soly in water at 17°: 0.38 g/l. LD50 orally in rats: 1000 mg/kg (Bailey, White).

Use

Plant growth regulator.